


Just Some Friendly Drinks

by TigStripe



Category: Supergirl (TV 2015)
Genre: First Kiss, Fluff and Angst, Friends to Lovers, Jealousy, Love Confessions, M/M, Mutual Pining, One Shot, Pining, Secret Crush
Language: English
Status: Completed
Published: 2020-07-30
Updated: 2020-07-30
Packaged: 2021-03-05 22:14:57
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,267
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25602670
Author URL: https://archiveofourown.org/users/TigStripe/pseuds/TigStripe
Summary: James finally gets Winn to agree to drinks after a patrol shift at the little piano bar down town. James wants to spend time with Winn, while Winn is more concerned with fawning over the pianist.
Relationships: James "Jimmy" Olsen/Winn Schott Jr.
Comments: 5
Kudos: 22





	Just Some Friendly Drinks

It was almost nine in the evening. The sun had already gone down, casting the city into its dazzling darkness of street lights and skyscraper signs. Most people would be at home, but the shadier side of society had made itself known tonight. As such, a response was needed.

Somewhere anonymous, an unobtrusive van sat parked silently, no lights or sounds indicating anyone was inside. But inside-

“Behind you.”

The cameras swiveled around as their owner spun in place and delivered a jaw-shattering jab to his encroaching assailant. They went down hard, a metal pipe clattering to the ground at their feet.

“Oof.” The man in the van cringed. “How does that not hurt your hand?”

“I took lessons,” his partner said through comms. “Plus, you know, padded and armored gloves.”

“I’m not seeing any movement on cams. Everything okay out there, James?”

“Yep. Everyone’s down.”

“Okay, then! Good work. Snag that bag o’ goodies and c’mon back.”

“On my way. Oh, and Winn? Thanks.”

“Aw. For what?”

“I didn’t see that last guy at all. Saved me from a beating.”

Winn waved a hand dismissively, knowing full well James couldn’t see it. “You would have taken him out eventually.”

The comms went silent as James went about his business as Guardian and Winn made preparations to collect him. He fastened his chair to the desk, threw down the entry ramp out the back door, and made sure the holster tracks along the floor of the van were cleared. Last time, he’d let something block the track and James’s motorcycle nearly bumped its way back down the ramp. It reminded Winn of the last time he’d attempted a pull-up.

It didn’t take James to get back to the van, and soon he came roaring up and into position, with Winn at the foot of the ramp, waiting for the engine to turn off before he lifted the ramp back into place.

As he did so, James took off his helmet and collapsed onto the edge of the van’s rear opening, his legs almost dangling to the road beneath. He flashed a dazzling smile in the dark, his teeth the most apparent feature of his face in the low light. “Ready to go?” he asked.

Winn didn’t look at him as he secured the ramp in place. “Go?”

“We said we’d go for drinks after the job tonight. Take a breather.”

Ah, yes. It had been James’ idea. Winn wasn’t against it, but he didn’t see a big point to it, either. “I guess? Do we have to?”

The smile disappeared. “Well, no. We don’t. But I thought it would be nice.” When Winn didn’t say anything, he tried again. “We could go to that piano bar you like.”

Winn perked up at this, bringing the smile back to James’s face. “Julia’s? Why didn’t you say so?”

“You just like watching Julia play,” James accused.

Winn laughed. “Well  _ yeah, _ have you seen her?” He hopped up into the van. “Okay, partner, let’s go!”

James’s face fell a little. Of course  _ Julia _ was what got Winn to go. But, hey, drinks are drinks, right?

Winn climbed into the front seat and started up the van as James changed out of his armor. The bar wasn’t too far, but they couldn’t go wearing just anything. The van was aimed at the Watchtower, where everyone had changes of clothes and even some more formal get-ups for infiltration missions. 

As they drove on, time stretched out as the thought of Winn fawning over the pianist all night made James shiver. He was aware of his ulterior motives of asking his partner out for drinks, and Julia was an obstacle to that plan. But maybe it would be worth it to see Winn excited over something. His energy was infectious and brought a smile to James’s face.

Before long, James stood near the exit to the Watchtower, waiting for Winn to finish changing. When he appeared from the bathroom, James couldn’t help but smile. He’d slicked up his hair a bit and donned a dinner jacket over nice jeans. It was a quaint, cute look.

He caught James staring. “You okay, bud?”

James shook himself out of his reverie. “No. Yeah. Fine. You ready to go?” He turned to exit, but a whistle from behind him stopped him in his tracks.

“Are those slacks new?” Winn asked.

Confused, James looked down at himself. He’d chosen a plum button-down dress shirt that hugged his shoulders and accentuated the taper of his back, leading down into typical black dress slacks. But he’d definitely worn similar around CatCo or out on the town with his friends before. He turned back to his partner. “What?”

“You look  _ good. _ The way the pants accentuate your, uh-”

James raised an eyebrow.

Winn gave a one-shouldered shrug, trying to play off his comment. “You could totally be an underwear model with a build like that.”

“Did a bit of that in college, actually.” James laughed at the slight jaw drop that accompanied this statement.

Winn cleared his throat, his cheeks slightly pink. “Okay, enough building up your confidence. It’s not like  _ you  _ need  _ me  _ to tell you how attractive you are.”

The skipped heartbeat and loud thump in James’s ears said otherwise.

“Well, you look great, too,” he said, trying his best to hide the waver in his voice. “Casual-chic. It’s cute.”

A small smile flashed across Winn’s face, but it soon fell into disappointment as he picked at his jacket. “I hate being cute.”

James struggled against the Heavens themselves to not blurt out how hot he thought Winn was, with his confident smile, his technical prowess, and his well-kept physique. Instead, he moved up to his friend and gave him the bro-iest of side hugs he could muster. He was the perfect height to kiss Winn on the side of the head - but he didn’t. “Let’s go get Julia to notice you, huh, pal?”

They arrived at the bar within the hour, and soon found themselves sitting in a corner booth with full view of the stage and main floor. It wasn’t crowded - the normal crowd was probably on its way - and the gentle sounds from the piano at the front of the room created a soothing, relaxed atmosphere.

They ordered their drinks and sat in contented silence as Winn stared longingly at the pianist, a lovely brunette in a floor-length sequined gown, sighing with little hearts in his eyes. James leaned back and watched the room, occasionally noticing the stares of other patrons. Mostly women. James would sometimes wave a polite finger or two at them when he noticed them, which usually got them to turn around or smile. Knowing everyone’s eyes were on him didn’t matter, though - the only set of peepers he cared about were aimed at the wrong person.

About the time Julia started her final piece of her set, Winn got up to go to the bathroom. James sat alone, his lack of partner drawing even more attention than before. He waved off a curious male suitor and turned down the drinks of an anonymous donor. Each time he received a flirty gaze or seductive smile, the burning in his chest grew.

He didn’t want to be here. He was only here because Winn wouldn’t go out for drinks with him anywhere else.

Before he knew what had happened, the piano had stopped, Julia’s set finished. She made her way off the stage and behind the curtain just long enough to grab a purse. She bowed her head to any applause that met her as she made her way across the bar, coming to stand directly in front of James’s table.

“You sounded great tonight,” James said, obviously on auto-pilot. He  _ especially _ didn’t want to talk to Julia, of all people.

She gave him a warm, sad smile. “Where’s your friend?”

Huh? “He’s in the bathroom. He’ll be back soon.”

She placed a gentle hand on the table to grab his attention. “I’ll be quick, then.”

Oh. Her, too? “Listen-” James started, but she shook her head.

“I know you’re not interested in me. I’ve been watching you. You were almost as fixated on your little friend as he was on me.”

He leaned forward, eyes locked on hers. “Okay, and?”

“But you didn’t look at him the same way he looked at me. He looked at me with the puppy dog, love-at-first-sight eyes. You looked at him with sadness and respect. Of hurt. Of longing.” Julia’s lips curled into a much more content, happy smile. “It was love.”

James sighed and averted his eyes. When he decided he wasn’t going to say anything, he shrugged.

“You should tell him.”

His eyes shot up to glare at her. “Sorry? And why should I do that?”

“Because life is too short not to. Either it works for you, or you get to move on.”

A valid point, but who was she to tell him-

“Miss Julia?”

Julia turned to see Winn grinning from ear to ear. James sunk in his seat.

“Yes?”

“You were amazing tonight. I-”

“Thank you. I’m afraid I have to go get ready for the next set. Please, dear, have a seat. Enjoy the show.” She turned and sauntered off, but instead of heading for the stage, she disappeared behind the bar, into the back room. James couldn’t help but wonder if that was intentional.

Winn plopped down next to James, his chin leaning on his hands like a schoolboy. James was pretty sure he could feel the wind of his legs kicking the air under the table. He couldn’t help but smile a little.

“Wait, where’d Julia go?” Winn asked, looking around. “I thought she said she was getting ready for her set.”

James didn’t answer. He was pretty sure he knew - Julia was watching them from somewhere safe, expecting him to follow her advice. He crossed his arms in front of him and sighed. Did he dare? Her logic  _ was _ sound; either he needed to confront these feelings, or move on from them. Winn was his friend and partner. He’d understand. After all, he’d pined after Kara way back when. He knew what James was going through.

“I think I’m about ready to go,” James said.

Winn pouted for a moment. “Really?” He shrugged. “Okay, sure. We got to hear one set. Have a few drinks. It was fun, right?”

James looked away and started to get out of the booth. “Yeah. A blast.”

They paid their tab and made their way outside, where James took a deep breath of crisp night air, hands in his pockets. It felt nice on his skin.

Winn sidled up beside him on the sidewalk, hands in his own pockets. They stood there, side to side, in silence for a solid minute, listening to the sounds of the nighttime city.

Finally, Winn broke the silence. “Penny for your thoughts?”

His thoughts? There were millions, most of which revolved around how irritated he was at Julia for sticking her nose into his business, but Winn didn’t need to know that.

“James. C’mon. Something’s bugging you.”

“Nothing’s bugging me.”

“Was it Julia? Did she come onto you or something?”

This was enough to evoke a response. James looked down at his friend with confusion laced across his brow. “What? No.”

Winn took a deep breath. “It’s okay. You don’t have to protect me. We’ve liked the same girl before. I can take it. But, I mean, you got Kara last time, so maybe this time I-”

“This isn’t even about Julia,” James snapped. He straightened up to his full height the moment the words escaped his lips. This was not how this was supposed to go!

Winn looked up at him in confusion. “Okay, so some other girl? But why was Julia talking with you?”

“She, uh-”  _ Think fast, Olsen! Say something!  _ “She thought you were cute.”  _ Not that! _

Winn shook his head. “Nah, I don’t buy that. She scurried off the moment I got there. No, this has to do with you.”

James felt Winn’s beady gaze scouring his face for answers. He was really persistent when he wanted to be.

“Just be straight with me, James. It’s not like it would be surprising that she took a liking to you. You’re tall, dark, and handsome. I’m…” He gestured to himself, as if proving a point.

The universe was determined to make him feel like an asshole, wasn’t it? James fought with ever fiber of his being not to say anything. as Winn sat on the curb and put his head in his hands. He wanted to scoop his little buddy up in his arms and tell him how amazing he was. How wrong he had it. 

Instead, he just sat down on the curb next to him.

“It’s so funny,” Winn said into his fingers. “I’m confident. I’m funny. I’m friggin’ smart. I’m cute. Everyone always says to just ‘be confident!’ or ‘be yourself!’ But when it comes to women, I’m always last pick.” He sighed as James’s heart sank further into his stomach. “Who would want  _ me _ when I’m standing next to  _ you?” _

“Me.”

The word has slipped out, sending ice through James’s veins. The night air became even more chilled, more still. He felt Winn’s confused eyes on him again.

“Very funny,” his friend said. “You want me with you so you look better in comparison.”

James let his eyes fall to the ground in front of him. “Stop. Stop talking like that.”

“It’s true, isn’t it?”

James finally looked over at Winn, their eyes catching the light of the bar signs overhead. “I don’t care about the women drooling over me.”

Winn gave a sardonic huff. “That’s cold, Jimmy. Thinking of them like that is only going to get you in trouble-”

“I care about you.”

The ice in his veins dispersed. He felt the tips of his fingers again. His tongue went back to being its normal size. His vision cleared. He stared directly into Winn’s, whose confusion only multiplied.

When Winn spoke, his voice broke. “What?”

James finally looked away, down at his hands. “I really care about you, Winn. I wish you’d stop talking about yourself like you’re less than me. You’re amazing. You’re smart. You’re funny. You’re charming. You’re cute. You look great in anything-”

“Wait,” Winn said, leaning away and pointing. “This sounds a lot like a confession of-”

“I’m in love with you, Winn.”

Winn was on his feet in the blink of an eye, one hand covering his agape mouth and the other pointing in accusation at James.  _ “No!  _ No! You’re  _ not _ in love with me! You  _ can’t _ be!”

James hitched an eyebrow at this response. A little dramatic for his tastes. “Not the response I was expecting, but okay, I’ll bite. Why not?”

Winn’s hands had gone from their shocked positions to a more awkward, shuffly one, rubbing his elbow as he averted his gaze. James looked up at him in a mixture of curiosity, confusion, and concern.

“Tell me you’re joking, please,” Winn whispered, not looking at him.

“I’m not joking.”

Winn gave a little shrug as he moved off a little bit, away from the bar. “You remember when you were a kid and you had a crush on someone, but you thought they were interested in someone else, or out of your league, or just not interested, so you forced yourself to get over them?”

Of course. Everyone had one of those. James didn’t say anything.

“I’ve had to do that a lot over the years. Especially after meeting Kara.” He cleared his throat. “You were all three: you had Kara, you’re  _ gorgeous, _ and I didn’t even know if you were into guys. Once my jealousy with Kara wore off, I think some time around the time you two broke up, I started  _ noticing _ you. And telling myself you were just a friend. A very, very hot friend. One who was only into girls.”

It took a moment for James to realize he was gawking. He shook himself out of it and stood up. “So you mean-”

Winn chuckled. It was a sad laugh. “Yeah. I was in love with you, too, and I told myself there was no way it’d ever happen. So I moved on.”

“Winn, I-”

“That’s why it’s so frustrating that you’d admit it to me now.” Winn looked up at him. A tear threatened to fall down one cheek, but it never quite got moving. “When did you realize it?”

James thought for a moment, but in his current, mildly panicked state, he couldn’t pinpoint a specific moment. “Does that matter?”

Winn’s face fell as he considered the question. “I guess not.”

James reached out and took Winn by the hand, leading him back to sit with him on the curb. “Listen. I’m sorry you went through that. It’s a big deal. But I’m here now. With you.”

The tear finally fell down Winn’s cheek. He wiped it away with a sniffle. “I don’t know. It feels like I had my shot and I blew it.”

“No, Winn.  _ This _ is your shot. It’s  _ my _ shot. We have an opportunity here.”

“It just brings back so many painful memories. The pining. The longing. The, uh-” Winn shifted uncomfortably. “The masturbating.”

James couldn’t help but chuckle. “Really? Just like that? Getting down to brass tacks, huh?”

“I’m sorry, but have you looked in a mirror lately?” Winn asked. They laughed, and it was the first open and honest laugh they’d had together all night.

James leaned over and put his head up against Winn’s. “I might have a history as an underwear model and have a personal best bench of over two-fifty, but that doesn’t make you any less amazing or attractive. I wanted to tear that jacket off of you the moment I saw you in it. Your shirts do amazing things to your chest. And-” He reached up and pinched Winn on the front of the chin. “-that  _ chin _ does things to me you wouldn’t believe.”

They sat in silence for a moment, each one just soaking in the present.

Winn spoke up. “So, we’re really doing this, then?”

James sat straight up and looked at him as profoundly as he could. He wasn’t quite sure how to make a “profound” face, but he put on a serious expression just the same. “Only if you want to.”

Pink peeked onto Winn’s cheeks moments before he leaned forward and tentatively met James’s lips with his. Tingling erupted up and down James’s face, neck, and back. He leaned into it, savoring the soft touch for as long as he could. It was a simple kiss, no tongue or teeth, but it meant the world to him to be trusted after all that.

When they broke away, James was the one blushing. “Wow. That was-”

Winn’s face screwed into his infamous joking expression. “Did you get the tingling, too, or am I a mutant?”

“No, there was definitely some tingling. But, you know, maybe we should try again, just to confirm.”

“Oh, so, for like, science.”

“For science.”

As they leaned in once again, they were oblivious to the sequined woman watching from the bar entrance, arms crossed confidently in front of her. She smiled and shook her hair back behind her should.  _ Told ya, _ she thought to herself as she turned to head back inside. She’d leave them to their own devices now. 

After all, it was a brand new night for both of them.


End file.
